Happy Friday, I’m Dylan Byers.

Welcome back to In The Room, my biweekly private email on the inner workings of the American media industry. Today, some never-before-reported backstory on the contentious—and nearly litigious—relationship between Politico’s former owner Robert Allbritton and his longtime C.E.O. Fred Ryan, which may help to explain a few of the former’s cutting remarks about the latter in a recent New Yorker assessment of Ryan’s current tenure at The Washington Post.

But first, a more current scoop: I’m told that when former President Donald Trump embarks on his campaign tour through New Hampshire and South Carolina this Saturday, he’ll be bringing with him on the plane a number of journalists from the nation’s top news outlets, including Kristen Holmes of CNN and Marc Caputo of NBC News, as well as reporters from print and digital outlets like The Wall Street Journal and Politico. The presence of journalists on Trump Force One portends a possible return to the old status quo, circa 2015, and a decision by most mainstream news organizations to cover Trump as a conventional candidate—and pay the high-cost travel fees—regardless of the January 6 Committee’s findings that he engaged in a conspiracy to overturn a lawful election.

The New Yorker piece was merely the latest meditation on the turmoil. As I’ve been reporting since last summer, many current and former Post employees blame Ryan, fairly or not, for failing to sustain the paper’s growth in the post-Trump, post-Marty Baron era and, more broadly, blame him for failing to transform the politics-centric Beltway journal into a multifaceted, always-on lifestyle content friendly holding company, à la The New York Times—a failure that has resulted in revenue shortfalls, leadership tensions, a talent exodus, a relatively small round of layoffs and, most recently, a surprise visit from the paper’s owner, Jeff Bezos.

As the New Yorker noted, the Times is now a full-fledged multi-media company while the Post remains a news-gathering organization—a polite yet significant distinction. But the real gripe has less to do with structure and economics than power and glory. Washington, after all, isn’t a big money town, like New York or San Francisco or Los Angeles. Instead, it’s the province of prestige and influence, its own regal court. At the Post, people are pissed because their product is discernibly less influential than it was a few years ago, and they hold Ryan responsible.

The article, written by Clare Malone, touched on almost all the familiar aspects of the Post’s ongoing drama. But what was most notable, at least to the insular and self-obsessed world of D.C. media, where everyone knows everyone, were a pair of cutting on-the-record remarks that Allbriton made about Ryan. After all, the two men go back decades: Ryan, a post-presidential chief of staff to Ronald Reagan, had joined the Allbritton family broadcast media empire as president and C.O.O., in 1995, not long after Allbritton graduated from Wesleyan. Ryan managed a portfolio of ABC-affiliated broadcast and cable stations that the family would ultimately sell to Sinclair Broadcast Group for nearly $1 billion. In 2007, Ryan also became the founding C.E.O. and president of Politico, the upstart political media company that Allbritton bankrolled and ultimately sold to Axel Springer for more than $1 billion just a little more than a year ago.

Allbritton may have been trying to help Ryan, as he told me, but it didn’t quite come off that way. In the first quote, Allbritton seemed to pile on Ryan for a recent botched layoff announcement in which the Post chief abruptly and petulantly stormed out of a town hall while refusing to answer questions. Allbritton called it “a very rare window into Fred when he gets frustrated.”

But it was the second quote, in particular, that really raised eyebrows. Allbritton, whom the stork deposited into a life of extraordinary fortune, portrayed Ryan as a courtier who had overseen his businesses rather than a savvy media executive, operator, and partner—a sort of high-end butler to his various powerful bosses, the Jeeves to many a Bertie Wooster. “Fred is very good at managing up,” Allbritton was quoted as saying. “He’s the perfect ambassador for a multibillionaire.”

It was the ultimate pat on the head, both patronizing and condescending, and yet it landed with more than a dollop of truth to some Beltway detractors. The quote seemed to underscore certain prevailing criticisms of Ryan’s leadership: that he is too focused on appeasing Bezos to formulate a bold vision for the paper’s future; that he moves too cautiously; that he enjoys the title and the status it confers but isn’t necessarily adept at managing all aspects of the business; that he isn’t a visionary.

Despite his chuckle, even Allbritton knew that the quote did not make Ryan look good, though he says he intended no ill will. “I guess no good deed goes unpunished,” Allbritton told me after saying that he had been trying to help Ryan. He also said he and Ryan were on very good terms, spoke often, and served on multiple boards together. He even took credit for convincing Ryan to talk to Malone for the piece.

But sources who know both men saw evidence of something else in those quotes: a scarred and contentious history that has not been reported until now, and that continues to affect their relationship to this day, even if they don’t show it. “Fred and Robert hate each other,” one of those sources told me. (Ryan declined to comment for this piece.)

The Allbritton television portfolio soon expanded to include six additional ABC affiliates across as many states, as well as Washington’s 24-hour news station NewsChannel 8, creating an empire that would allow Allbritton to eventually take over Riggs Bank, a depository for wealthy foreign clients that eventually got mired in debt and dragged down in a Pinochet laundering scheme. (In 2005, the bank and Albritton family agreed to pay $9 million to Pinochet’s victims.)

In 2013, months after the elder Allbritton’s death, Robert tasked Ryan with orchestrating the sale of the television assets, which at that point were turning nearly $30 million in annual profits, according to someone familiar with the situation. Ostensibly taking stock of the consolidation in television and the rapid growth of digital, Allbritton declared that he wanted to invest more in assets like Politico, which was then just six years old but had already established itself as a powerful and disruptive force in political journalism. “This is the Golden Age of new media innovation, and I intend to stay on the leading edge of it,” he told his staff.

That July, Allbritton Communications sold its eight stations to Sinclair for $985 million. After accounting for about $455 million of debt, the sale left Allbritton with well over half a billion in cash. Per the terms of his employment agreement, Ryan was entitled to receive a small percentage of that sum, sources familiar with the matter said. But as the deal closed, Allbritton took on additional short-term debt, thereby reducing Ryan’s payout. Ryan’s payday ultimately came in millions of dollars under what he had anticipated, and he was livid about it. He engaged David Boies, the prominent and highly expensive super lawyer.

Alas, these sorts of disputes are always sticky. Multi-billionaires, of course, are surrounded by armadas of deal lawyers, trust and estate attorneys, and tax specialists who are incentivized handsomely to defend their client’s every dollar. Their ambassadors, alas, are mere mortals who cannot be blamed for viewing this cold-hearted reality for what it is: extremely shitty. And while they may be able to hire multi-thousand-dollar-an-hour super lawyers to send a shot across the bow, they themselves are not generationally wealthy and must consider the impact of an asymmetrical legal battle on their long term economic future. At the eleventh hour, sources said, Ryan decided not to move forward with a legal claim.

But that September, less than two months after the sale to Sinclair, Ryan announced that he would be stepping down to “pursue other career options.” Ever the savvy operator, Ryan showed total gratitude toward Allbritton in his farewell memo, describing him as “my friend and collaborator for nearly two decades.” In Washington, everything is politics.

On our phone call, Allbritton confirmed that Ryan had threatened to file a lawsuit against him over the sale of the television assets, but he dismissed it as water under the bridge: “that happened a decade ago,” he said. “There’s no bad blood there.” Others who have some insight into their relationship see it differently and said that, while Ryan and Allbritton may like to be seen as being on good terms, they both harbor a lot of antipathy toward one another. According to one person familiar with the dynamic, Allbritton and his mother complained that Ryan had “moved to the neighborhood” when he bought a home in Georgetown years later.

Four months after announcing his departure from Politico, Ryan was at the annual Alfalfa Club Dinner, the black-tie event for the Washington elite, where he was seated next to Jean Case, wife of the billionaire AOL visionary and venture capitalist Steve Case. According to Malone’s report in The New Yorker, Jean Case asked him what he wanted to do next and he told her that he wanted to be the publisher of the Post, which Bezos had bought just a few months earlier. The Cases reportedly brokered a meeting, and Ryan got the job later that year. And by all accounts, despite his recent reversal of fortunes at the paper, Ryan remains in Bezos’s good graces—perhaps for the reason Allbritton suggested. Or perhaps because, lest his charges forget, Ryan engineered a plan that helped reverse the Post’s fortunes from a post-prime asset into, once again, an international icon.

Coincidentally enough, this year’s annual Alfalfa Club Dinner takes place this weekend, starting with a pre-dinner dinner on Friday night, the official dinner at the Capitol Hilton on Saturday, and a brunch, at Robert’s mother’s house, on Sunday. Ryan and Allbritton will be in attendance for all three, in the company of more than two hundred of the nation’s most venerable political leaders, cabinet members, joint chiefs, Supreme Court justices, and prominent business executives—though Bezos, Ryan’s current boss, is expected to miss the dinner this year.

Of course, Ryan and Allbritton will likely be preoccupied with the weekend’s festivities: jocular speeches from David Rubenstein, the outgoing club president, and Jim Mattis, the incoming one; the induction of new club members such as Nancy Pelosi and Gina Raimondo (the club only started accepting women in 1994, when Hillary broke the barrier) as well as Microsoft chief Satya Nadella. But on the off chance that Ryan and Allbritton do run into one another and get a few minutes to themselves, perhaps they’ll dwell, if only for a moment, on the past.